Kyle Wiggs / Writing

Writing

Leadership

Building companies, leading people, and an honest account of what endurance sport teaches.

12 pieces

Leadership

What endurance sport does not teach you →

Every founder who has finished a long race wants to tell you it is like building a company. Most of that does not survive contact with either activity.

Leadership

Leading people who do not have to listen →

A team captaincy is the first job where the outcome depends on people under no obligation to do what you say. Most of leadership is that job.

Leadership

The order matters more than the decisions →

Three of the companies I have been part of exist because the previous one exposed a constraint it could not solve. That sequence was not planned and it was not accidental.

Leadership

The middle is where it gets decided →

The start is exciting and the end is satisfying. Almost everything that determines the outcome happens in a stretch that has neither quality.

Leadership

The co-founder conversation everyone postpones →

Four questions, all uncomfortable early and all catastrophic late. The discomfort does not decrease with time. The cost does increase.

Leadership

Naming the thing you are bad at →

It is the cheapest credibility available and it is almost never used, because it feels like it costs something.

Leadership

When you are the constraint →

It arrives quietly and it is genuinely hard to see from the inside, because from the inside it looks like being needed.

Leadership

The hardest judgement is when to stop →

Everything about founder culture trains persistence. Almost nothing trains the opposite judgement, which is required just as often.

Leadership

What I got wrong about scale →

Three things I believed early that did not hold. All three are common beliefs, which is partly why I held them.

Leadership

Why hiring people better than you is harder than it sounds →

Everyone agrees with this and comparatively few do it. The obstacle is not recognising the principle.

Leadership

Most recurring meetings are a missing decision →

A meeting that keeps happening about the same topic is usually not a communication problem. It is an ownership problem.

Leadership

Why write any of this down →

Publishing opinions in a regulated industry is a small amount of risk for a specific and worthwhile return.